200 Perfect Chicago Captions for Instagram + Chicago Quotes

Looking for the best Chicago Captions for Instagram or Chicago Quotes to go with your pics taken in Chicago? You’re in the right place my friend. Chicago is an epic city known for its harsh weather, artistic scene and the Bean, which is a huge Chicago icon. Obviously, there is so much more to Chicago! 

Whether you’re looking for Instagram captions for Chicago photos or inspirational or funny Chicago quotes, I’ve got you covered!

This page is a collection of the best clever captions about Chicago, including cute Chicago picture captions, Chicago captions puns and interesting, insightful quotes about Chicago. 

On a day that you don’t feel too creative, just pick one of the captions in this post, and you’re good as gold.

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Best Chicago Captions for Instagram 

Here are some of the best Chicago Captions, perfect to go with your photos on Instagram. If you don’t have much time, in this section, I gathered my favourite phrases, ready to be used with Instagram content about Chicago. Feel free yo copy and paste any caption that you like!

1. “Bright lights, city nights in Chicago.”
2. “Big cities can have big hearts too.”
3. “I fell in love, his name is Chicago.”
4. “Chicago, I’m coming for you.”
5. “Chicago is always a good idea.”
6. “Friends, drinks and Chi-Town.”
7. “All you need is love and skylines.”
8. “Chicago is calling and I must go.”
9. “Keep calm and go to Chicago.”
10. “My heart burns for the city lights.”
11. “Somewhere over the rainbow, you will find Chicago.”
12. “Chicago floats my boat.”
13. “Either you love Chicago or you are wrong.”
14. “The weather in Chicago really… blows me away.”
15. “Chicago is always on my mind.”
16. “I’m having an affair with Chicago.”
17. “I’m a Chicago girl.”
18. “Born and bred in Chicago.”
19. “Hello Chicago, your lights are fireflies in my heart.”
20. “Hello Chicago, you’re looking gorgeous today.”
21. “Dear Chicago, I will never get over you.”
22. “Once upon a time, in the enchanted land of Chicago.”
23. “I am here, but my heart is in chicago.”
24. “Started from the bottom, now we here.” (Skydeck)
25. “I love Chicago; it is unique in the world”

Short Chicago Instagram Captions 

Here are more Chicago Instagram captions that are short and sweet! No matter your style, I bet you can choose something that suits your Instagram account!

26. Chicago dreamin’
27. Chicago, you look great.
28. Welcome to Chicago.
29. Once upon a time in Chicago.
30. Sweet home Chicago.
31. Meet me in Chicago.
32. Meet me in Windy City.
33. Take me to Chicago.
34. Chicago let’s do it.
35. Windy Wednesday in Chicago. 
36. Views from the windy city.
37. Daydreaming in Chicago.
38. Cheers from Chicago!
39. Let the city set you free.
40. A concrete version of paradise.
41. Wanderlust and city dust.
42. My kind of town.
43. Live, love, Chicago.
44. You cannot stop Chicago.
45. P.S. I love Chicago.
46. Stuck in this Chicago loop.

Sayings about Chicago

In this section, you will find the best sayings about Chicago and how it feels to live in this incredible, vibrant city.

47. “The best views in Chicago are at Navy Peer.”
48. “Things ain’t so bad in the windy city.”
49. “Chicago is tough so are you.”
50. “You can leave Chicago, but it will never leave you.”
51. “Life’s better by the lake.”
52. “East or West, Chicago is the best.”
53. “Happiness is…. holding tickets that say Chicago.”
54. “Chicago shines even brighter at night.”
55. “Finally made it to Chicago. It’s a boat time!”
56. “I don’t keep calm I’m from Chicago.”
57. “You never forget your first day in Chicago.”
58. “The most American place in America, Chicago.”
59. “Make sure to relish the good times in Chicago.”
60. “Feelings come and go like clouds in the Windy City.”
61. “Once upon a time, in the enchanted land of Chicago”
62. “Follow your heart, even if it takes you all the way to Chicago.”
63. “Never seen something like Chicago before.”
64. “A bad day in Chicago, is still better than a good day anywhere else.”
65. “Wherever you go, go with all you are heart especially if you are in Chicago.”
66. “Chicago, the city where you can experience four seasons in one day.”
67. “I miss everything about Chicago, except January and February.”

Funny Chicago Captions

How good is your sense of humour? We all need more laughter in our lives, agreed? If you want to entertain your Instagram followers, choose one of the funny Chicago captions below.

68. “Lake hair, don’t care.”
69. “Just a cheesy selfie in Chicago.”
70. “In Chicago, I’m in the Loop.”
71. “Chicago stole a pizza of my heart.”
72. “What you talkin’ bout Willis Tower?”
73. “Chi chi cheese. We’re in Chicago!”
74. “I’m blown away by the Chicago skyline.”
75. “Lake Michigan is pretty Great.”
76. “Get blown away by the sights of the windy city.”
77. “The windy city is in my back pocket.”
78. “I love Chicago, but I’m ready to get the L out of here.”
79. “Dogs love Chicago because they get to visit Wiggly Field.”
80. “In a world filled with crazy, I hope you choose to live in Chicago.”
81. “You’d have to be a weir-mixture not to like Chicago Deep Dish.”
82. “Let minnow if you want to spend the day on Lake Michigan!”

Chicago PUNS Captions 

If you want to take your humour to another level, you will love this section! Choose one of the PUNS about Chicago below, and lots of laughter comes guaranteed! Which one is your favourite?

83. “Chi likes you a lot!”
84. “Slice, Slice baby!”
85. “Chicago food is a Weiner!”
86. “Chicago, I lake you a lot!”
87. “Having a Fields day in Chicago.”
88. “I never sausage a beautiful hot dog.”
89. “Let me be Frank, this is a tasty dog.”
90. ​​”Make sure to relish the good times in Chicago.”
91. “A trip to Chicago takes quite a bit of dough.”
92. “Pier pressure brought me here.” (Navy Pier)
93. “A trip to Chicago is an L-evated experience.”
94. “I love Chicago, but I’m ready to get the L out of here.”
95. “A day at Lake Michigan buoys my spirits!”
96. “Let’s be Frank, Chicago is always a good idea.”

Chicago Bean Captions for Instagram 

Are you looking for Chicago Bean captions? This iconic building is one of the most recognisable landmarks of the city. If you’ve got some cool photos of reels taken by it, choose one of the funny phrases about the Chicago Bean below!

97. “Chicago, where have you bean all my life.”
98. “Chicago, it’s bean real!”
99. “Cool beans.”
100. “Chicago: Bean there, done that.”
101. “Chicago’s frozen bean.”
102. “Just a couple of beanie babies.”
103. “I’ve never bean to Chicago before.”
104. “​​I bean thinkin’ about you Chicago.”
105. “You haven’t bean to Chicago unless you’ve bean here.”

Famous Chicago Quotes for Instagram

In this section, you will find some of the most famous Chicago quotes!

106. “This is my kind of town, Chicago is.” – Frank Sinatra

107. “There is none other quite like my City of Big Shoulders.” – Irv Kupcinet

108. “Let me tell you something. I’m from Chicago. I don’t break.” – Barack Obama

109. “Eventually, I think Chicago will be the most beautiful great city left in the world.” – Frank Lloyd Wright

110. “Perhaps the most typically American place in America.” – James Bryce

111. “In the twilight, it was a vision of power.” – Upton Sinclair 

112. “I have struck a city – a real city – and they call it Chicago.” – Rudyard Kipling

113. “It’s 106 miles to Chicago, we’ve got a full tank of gas, half a pack of cigarettes; it’s dark and we’re wearing sunglasses.” – Elwood Blues

114. “My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.” – Oprah Winfrey

115. “It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.” – Mark Twain

116. “It is the most perfect presentation of nineteenth-century individualistic industrialism I have ever seen. Chicago is one hoarse cry for discipline.” – H. G. Wells

117. “Chicago still remains a Mecca of the Midwest—people from both coasts are kind of amazed how good life is in Chicago, and what a good culture we’ve got. You can have a pretty wonderful artistic life and never leave Chicago.” – Harold Ramis

118. “Chicago is constantly auditioning for the world, determined that one day, on the streets of Barcelona, in Berlin’s cabarets, in the coffee shops of Istanbul, people will know and love us in our multidimensional glory, dream of us the way they dream of San Francisco and New York.” – Mary Schmich

118. “A city without illusions but with vaulting imaginations and expectations. A city of burning energies on the shore of a huge northern sea.” – Brian Doyle

Funny Quotes About Chicago

In this section, you will find humorous things famous people said about Chicago. Some are hilarious, other quotes are a little harsh. I’m curious to see if you agree or disagree with these opinions.

120. “Chicago – a pompous Milwaukee.” – Leonard Louis Levinson

121. “Chicago ain’t no sissy town.” – Hinky Dink Kenna

122. “You know what they say about Chicago. If you don’t like the weather, wait fifteen minutes.” – Ralph Kiner

123. “I think that’s how Chicago got started. A bunch of people in New York said, ‘Gee, I’m enjoying the crime and poverty, but it just isn’t cold enough. Let’s go west.” – Richard Jeni

124. “Hell has been described as a pocket edition of Chicago.” – Ashley Montagu

125. “I’d rather be a lamppost in Chicago than a millionaire in any other city.” – William A. Hulbert

126. “There is only one thing for Chicago to do, and that’s to move to a better neighborhood.” – Herman Fetzer

127. “Loving Chicago is like loving a woman with a broken nose.” – Nelson Algren

128. “Chicago is an October sort of city even in spring.” – Nelson Algren

129. “Chicago Cubs fans are ninety percent scar tissue.” – George F. Will

130. “In Chicago not only your vote counts, but all kinds of other votes-kids, dead folks, and so on.” – Dick Gregory

131. “I must confess a shameful secret: I love Chicago best in the cold.” – Erik Larson

132. Chicago is not the most corrupt American city. It’s the most theatrically corrupt.” – Studs Terkel

133. “They do things big, big I tells ya: Mike Ditka big. Michael Jordan big. Bill Murray big. Oprah! It’s one cultural Mount Everest after another.” – Anthony Bourdain

134. “Chicago is unique. It is the only completely corrupt city in America.” – Charles Merriam

135. “I warn you, Jedediah, you’re not gonna like it in Chicago. The wind comes howling in off the lake and gosh only knows if they ever heard of lobster Newburg.” – Orson Welles

136. “One of the hallmarks of Chicago is that we do so many things in an original manner. What other city has made a river flow backward? What other city makes traffic flow backward?” – Mike Royko

137. Chicago seems a big city instead of merely a large place.” – A.J. Liebling

138. “Chicago is not the most corrupt of cities. The state of New Jersey has a couple. Need we mention Nevada? Chicago, though, is the Big Daddy. Not more corrupt, just more theatrical, more colorful in its shadiness.” – Studs Terkel

Chicago Movie Quotes 

Have you watched any movies about Chicago? In this section, you will find the most famous Chicago movie quotes, perfect for those of you that love the cinema.

139. “Welcome to Chicago. This town stinks like a whorehouse at low tide.” – The Untouchables

140. ​​”Chicago happened slowly, like a migraine.” – Neil Gaiman, ‘American Gods’

141. “Six bucks and my right nut says we’re not landing in Chicago.” – Planes, Trains and Automobiles

142. “It’s 106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it’s dark… and we’re wearing sunglasses.” – The Blue Brothers

143. “He rules Chicago with absolute power. No one could touch him. No one could stop him.” – AL Capone

144. .”Let the worthy citizens of Chicago get their liquor the best way they can. I’m sick of the job-it’s a thankless one and full of grief. I’ve spent the best years of my life being a public benefactor.” – Al Capone

145. “Eliot Ness: I want to get Capone! I don’t know how to do it. – Jim Malone: You wanna know how to get Capone? They pull a knife, you pull a gun. He sends one of yours to the hospital, you send one of his to the morgue. That’s the Chicago way! And that’s how you get Capone!” – The Untouchables

146. “It’s a very bad sign when a cop thinks that Chicago will fall apart without him.” – Running Scared

147. “Back in Chicago, all we cared about was Rock ‘n’ Roll and staying out of the army.” – John Belushi 

148. “I’m going to do all my movies here in Chicago. The Tribune referred to me as a ‘former Chicagoan’. As if, to do anything, I have to leave Chicago. I never left. I worked until I was 29 at the Leo Burnett advertising agency, and then I quit to do this. This is a working city, where people go to their jobs and raise their kids and live their lives.” – John Hughes

148. “One of the problems with people in Chicago, she remembered, was that they were never lonely at the same time.” – Lorrie Moore, ‘Birds Of America’

Quotes On Chicago Expressing Admiration

Here are the most positive Chicago quotes from people that deeply love and admire the city. Can you relate to any of these opinions?

150. “Going to Chicago was like going out of the world.” – Muddy Waters

151. “Chicago has disappointed her enemies and astonished the world.” – Erik Larson

152. “The people of Chicago are a proud people – and for good reason.” – Jane Byrne.

153. “We’re Chicago – we can do anything, damn it.” – Elva Rubio

154. “It’s wonderful to be here in the great state of Chicago.” – Dan Quayle

155. “The best food is in Chicago. There are great restaurants everywhere, from fancy places to burger joints.” – Steve Carell

156. “You’d never think of taking a cab if you had to walk a mile down Chicago’s Michigan Avenue.” — Helmut Jahn

157. “It’s a bustling metropolis with the warmth of a small town; where the world already comes together every day to live and work and reach for a dream.” – Barack Obama.

158. “Chicago does not go to the world, the world comes to Chicago!” – Peter Orner

159. “Chicago will give you a chance. The sporting spirit is the spirit of Chicago.” – Lincoln Steffens

160. “It is wonderful to be here in the great state of Chicago.” – Dan Quayle

161. “But when I go to Chicago, I know I’m home.” – Hank Sauer

162. “I adore Chicago. It is the pulse of America.” – Sarah Bernhardt

163. “Theater in Chicago will always be my first love.” – William Petersen

164. “Chicago’s neighborhoods have always been the city’s greatest strength.” – Jane Byrne

165. “I’m impressed with the people from Chicago. Hollywood is hype. New York is talk. Chicago is work.” – Michael Douglas

166. “It’s one of the greatest cities on the planet. My heart beats differently when I’m in Chicago. It slows down and I feel more at ease.” – Jeremy Piven

167. “Anywhere in the world, you hear a Chicago bluesman play, it’s a Chicago sound born and bred.” – Ralph Metcalfe

168. “I love Chicago; it is unique in the world. So much intellect, so many artistic voices – it has fantastic potential (as an Olympic candidate).” – Jerome Sans

169. “A roaring city, gunfire and applause and thunder. Gleaming but made of bone and stone.” – Brian Doyle

170. “Sometimes words are just music themselves. Like ‘Chicago’ is a very musical sounding name.” – Tom Waits

171. “Chicago is partly a fairy tale because it’s inside one person’s head, so that part of it’s made up and the rest of it is reality.” – Colleen Atwood

172. “Chicago, mistress of the lakes, controller of our inland trade, the freest city of our states, what wondrous strides thy fame has made!” – Charles Frederick White

Unique Chi Town Quotes 

173. “Chicago has a strange metaphysical elegance of death about it.” – Claes Oldenburg

174. “A city that was to forge out of steel and blood-red neon its own peculiar wilderness.” – Nelson Algren

175. “Chicago is the product of modern capitalism, and, like other great commercial centers, is unfit for human habitation.”  – Eugene Debs

176. “Chicago sounds rough to the maker of verse. One comfort we have – Cincinnati sounds worse.” – Oliver Wendell Holmes

177. “Chicago has so much excellent architecture that they feel obliged to tear some of it down now and then and erect terrible buildings just to help us all appreciate the good stuff.” – Audrey Niffenegger

178. “Chicago is a city of contradictions, of private visions haphazardly overlaid and linked together. If the city was unhappy with itself yesterday-and invariably it was-it will reinvent itself today.” – Pat Colander

179. “Chicago is where the whole idea of community policing began.” – Mayor Rahm Emanuel

180. “Until 1974, it was actually illegal to appear in public in Chicago if you were ugly.” – Scott Matthews

181. “Chicago is a sort of journalistic Yellowstone Park, offering haven to a last herd of fantastic bravos.” – Ben Hecht

182. “You can have a pretty wonderful artistic life and never leave Chicago.” – Harold Ramis

183. No realistic, sane person goes around Chicago without protection.” – Saul Bellow

More Chicago Sayings Quotes

184. “Chicago is a town, a city that doesn’t ever have to measure itself against any other city. Other places have to measure themselves against it. It’s big, it’s outgoing, it’s tough, it’s opinionated, and everybody’s got a story.” –Anthony Bourdain 

185. “A lot of real Chicago lives in the neighborhood taverns. It is the mixed German and Irish and Polish gift to the city, a bit of the old country grafted into a strong new plant in the new.” – Bill Granger

186. “I just wanted to see every single musical I could. The very first one I saw was ‘Beauty and the Beast’, the only one I could get a ticket for, and then ‘Les Miserables’ and then ‘Chicago’.” – America Ferrera

187. “That weekend the city blushed with a great heat wave but on Monday it rained, cooling the ache in the street’s burn.” – Daniel Amory

188. “I am an organic Chicagoan. Living there has given me a multiplicity of characters to aspire for. I hope to live there the rest of my days.” – Gwendolyn Brooks

189. “…a city that was to live by night after the wilderness had passed. A city that was to forge out of steel and blood-red neon its own peculiar wilderness.” – Nelson Algren

190. “A facade of skyscrapers facing a lake and behind the facade, every type of dubiousness.” — E.M. Forster

191. “I give you Chicago. It is not London and Harvard. It is not Paris and buttermilk. It is American in every chitling and sparerib. It is alive from snout to tail.” – H. L. Mencken

192. “Being Irish was a big thing for me, particularly growing up in Chicago.” – Lara Flynn Boyle

193. “Blessed are the people of Chicago, and blessed the strangers in their midst, in the article of malt liquor; for it is excellent, it is honest, and it is abundant.” – James Parton, ‘Atlantic Monthly’

193. “After three years in Chicago, I decided to call it a career.” – Ted Lindsay

195. “Guys, you’re Chicago. You’re the home of Laurie Metcalf and Jessie Mueller and Steppenwolf. And a million, a million, a million brilliant theater practitioners.” — Lin-Manuel Miranda

196. “There seems to be a different Chicago around every street corner, behind every bar, and within every apartment, two-flat, cottage, or bungalow. City of immigrants or city of heartless plutocrats, say what you will, Chicago almost defies interpretation. In many ways, Chicago is like a snake that sheds its skin every thirty years or so and puts on a new coat to conform to a new reality.” – Dominic A. Pacyga

196. “If man is, or is searching to be, omnipotent, I am willing to accept Chicago’s gigantism; but I should like the opposite to be accepted as well: a city which would fit in the hollow of one’s hand.” – Jean Genet.

198. “Out in Chicago, the only genuinely civilized city in the New World, they take the fine arts seriously and get into such frets and excitements about them as are raised nowhere else save by baseball, political treachery, foreign wars, and romantic loves . . . almost one fancies the world bumped by a flying asteroid, and the Chicago River suddenly turned into the Seine.” – Henry Mencken

199. “Chicago is a city where the practical and the inspirational exist in harmony; where visionaries who made no small plans rebuilt after a great fire and taught the world to reach new heights. It’s a bustling metropolis with the warmth of a small town; where the world already comes together every day to live and work and reach for a dream—a dream that no matter who we are, where we come from; no matter what we look like or what hand life has dealt us; with hard work, and discipline, and dedication, we can make it if we try.” – Barack Obama

200. “We struck the home trail now, and in a few hours were in that astonishing Chicago – a city where they are always rubbing a lamp, and fetching up the genii, and contriving and achieving new impossibilities.” – Mark Twain, ‘Life On The Mississippi’.

Final Word

I hope you enjoyed this collection of Chicago captions for Instagram! Chicago is such a fantastic, vibrant and multicultural city – a perfect destination to visit!

If you’re looking for more inspiration, meet me on Instagram!

Mal xxx

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